Judging by the second picture, you spent time on Michigan Ave in summer, which is not the best place to look for fashion, any more than Fifth Avenue in NYC during Christmas. We’ll try and pull it together in time for your winter visit.

BTW, love the blog. After reading it I hold myself to a higher standard every time I leave the house.

I grew up in Chicago and I am consistently disappointed with the state of fashion there. For a town with such sophisticated taste in architecture and design, for some reason personal appearance is left out in the cold.

Well in defense of Chicago, it was hot, really hot, and it’s hard to look good when you are melting.

It was also a tourist weekend, we had Lollapalooza, Tall Ships, a professional soccer game, and judging by the number of families walking around wearing jerseys and baseball hats, a baseball game as well. Like most city dwellers, when that happens everyone gets testy and no one wants to go outside.

Well, as a lifetime chicagoan, I’ll chalk it up to one more thing (aside from the heat, the tourists for lolla, etc…) – the stores you were at were absolutely 100% an older, solely Gold Coast crowd (except Jake, which you didn’t mention, but I hope you stopped at).

The boutiques in the East Village, Wicker Park and Bucktown areas (around Chicago, Damen, North, and Armitage) have incredible stuff, and the people who shop and work there reflect that style. Habit immediately comes to mind, Helen Yi, p45, Niche and City Soles. . .

I have always been a fan of Chicago style too. But heatwaves can suck the life out of anything.

Seattle could benefit from your watchful eye. The Emerald City is notoriously casual and defiantly so. The rumors are true: Folks attend the opera in polar fleece zip vests and keen sandals. Summer is a blur of short cargo shorts and camisoles with flip-flops…at work.

Do you think their lack of attention to you was because you were male in the women’s section and they figured men don’t buy clothes for women? Its a shame since they lost a potential sale or even just a recommendation to a female friend.

As a man, I’ve noticed that when following around girlfriends in the women’s sections I suddenly become invisible.

As a newcomer to Chicago, this is particularly interesting. I’ve actually been stunned by how good the service is, so I guess there’s no rhyme or reason to it. (Or maybe I’m coming from a low base!)

Mind you, I found an exception in Ikram. I felt instantly dismissed and have stubbornly refused to go back. (Did like their shoes though, dammit….)

I’ll go out on a limb now. I’m only new to Chicago and I’ve only visited New York a few times, but… on a day to day basis, I haven’t seen the variations of style here that I perceive in New York. (Okay, so I’m corporate and am probably skewed to seeing suits…. but that aside…)

But overall? Summer in Chicago seems to be a season for over made-up, over-tanned and way too much swimwear worn as daywear.

As a Chicagoan who loves this blog, I have to say your assessment is pretty accurate—on average we’re not really stylish people. While Chicago offers some good stores and options (this isn’t LA or NY but it isn’t Houston or Atlanta either), Chicagoans for the most part aren’t really interested in fashion. Though it is not for want of effort; the Mayor himself has set up a “fashion board” to help promote Chicago designers and we have a poorly attended and silly “fashion week” sponsored by Macy’s and a bunch of Chicago’s actually quite outstanding art and design schools. But that said: A shirt from Banana Republic and flip-flops and you’re basically dressed for any occasion. I still love it more than any other city in the country though. Plus, when I put on a tie after work I’m practically royalty!

Scott – I love your pictures and commentaries! It’s great seeing pictures of regular people – the kind we walk by and live with every day.

It’s funny that you mention the dearth of smaller sizes in the city. I myself make the suggestion to New Yorkers to go shopping out in the ‘burbs for exactly the same reason – the surplus of smaller sizes in less metropolitan areas.

If you’re looking for a laugh, take a look at my blog – the difficulties in being ridiculously small. I’d like to be beautifully dressed too, but sometimes just finding anything to wear is impossible for my 4’10″ self.

I was a little worried that you would not find a lot of good style here in Chicago. Also, I don’t think the plethora of small sizes is due to older ages; it’s the Chicago diet. Having said that, yeah, the fact that you were here in the hottest part of the summer didn’t help provide inspiring fashion photo opportunities.

Its the mid-west remember, all that fashion stuff is for you folks on the coast. If Chicago was not inspirational, then forget my Cincinnati. For the men, its bulbous khaki pants with blue or white shirts!

Are you saying that sizes 4 & 6 are the larger sizes, or that those are the sizes left because Chicago women are buying sizes 8 & 10? Personally, I don’t want to live in a world where 4 & 6 are considered large.

Unfortunately your inability to find many good shots is not due to being in Chicago on a Friday summer afternoon. This is the way it usually is. I had just emailed my sister in St. Petersburg regarding the dearth of fashion in the Windy City. This became clear after reading the Slate piece on yours and other sites. There are, I’m sure many people who have good/or unique fashion sense, but its really hard at times to find it. I work in the Loop and live off of Michigan Ave, which considering the stores available, you would think there would be more examples of stylish men and women.And before any Chicagoan gets their back up – yes I love Chicago and all it has to offer, but sorry when it comes to fashion/style on the street its just not there.

Next time you are in Chicago make sure it is a bit colder. That’s when we do our best! As a boutique owner I have to say that there is a HUGE fashion client here in both Men & Women. I really try to source out great lines and bring in amazing items and we have fantastic reaction. I think your element is great!!Pop in next time you are around!Best,Jim WetzelJake

That’s very true about Blake. Back when they were in Lincoln Park and carried menswear, this time of year would roll around and you’d find racks of Margiela 10, Raf Simons, Dries, and Ann Dem. in all sizes and marked down to 1/3 of the original price. It was pretty much cheaper to shop there on those brands than to go to the mall and buy Ralph Lauren or Banana Republic.

It’s too bad they eventually realized how unprofitable that section of the store was and put an end to it, because I had a good thing going for awhile…

The “polished” expectation is a value given to an idea of fashion, in spite of all humans being part of fashion. Maybe a modern mind in the look for class determination understand fashion as matter of some vs others…interesting comment reflecting the “understanding” of sartorial expression.

Well being a native of the chicago area (let alone the midwest) I must painfully agree that it wasn’t until I started going to school on the east coast that I discovered the beauty of true fashion. We have our good days, I just hope we get better.

“The guy at the top – I mean, c’mon, put the dreadlock sock away.”

To that I just say, that being a part of a caribbean family, one must be careful to remember that some things were of cultural significance to some before becoming a fad for everyone else.

Come on, Sart! I was excited that you were coming here, and though I fully admit Chicago is no New York, Paris, or Milan, but many Chicagoans can hold their own when it comes to fashion. I am surprised that this woman was the best representation of style you could find. I can see from the picture that you were on Michigan Ave., near Water Tower. That is where dowdy, unfortunate suburbanites congregate. Next time, I would suggest Wicker Park, Boystown, and perhaps the Loop during the lunch hour. In the menatime, we will try to improve! Love your blog.

the sartorialist: i hope you’re not offended i meant it in the best possible way! “polished” in the sense of quality photography and almost-incidental yet crisp accompanying words – this post seemed to me to be accompanied by a good deal shopper’s glee rather. it made for amusing reading.

no it’s not a reflection of my understanding of fashion. i’m hardly the sort to pontificate on fashion. :D

Wow. I thought that since you were from Chicago you would know that Michigan Ave in the middle of the summer was NOT the place to look for great fashion. Unless you were setting it up all along to make Chicago look like a place with no style sense. After Wicker Park, Bucktown,Ukranian Village, and any number of other places you could have visited, it seems suspicious that you would have chosen a spot that is well-known to be overrun with tourists as a representative of Chicago style. There are great boutiques, fabulous design talent and great dressers here. It is unfortunate that you arrived back here with preconceived ideas.

JenniferI think it is really funny that all the people from Chicago keep saying that Michigan Ave is all tourist and no style and yet the same could be said for 5th Ave in NYC but i get plenty of shots there.

Also Oak Street/ Rush St and Mich. Ave have all the big stores so some fashionable people must be going there.

By Wicker Park i think what you are really saying is that is where the young trendy people go but I don’t always look for just the young trendies

I remember Chicago as Ultimo and June Blaker and City. I know Chicago has style but I just didn’t see much when I was there but I’m sure I will be back soon for another look.

I moved to Chicago this year from a tiny hamlet in rural Michigan where haute couture was a Willi Smith castoff from TJ Maxx. I was thrilled to move to a real city with culture and fashion, but I must agree with posters who says Chicagoans are a very pragmatic, practical Midwest crowd who dress for the weather, not to impress. However, I have to say that relatively speaking, the shopping is FAR better than it is in Southwest Michigan. Imagine having to drive across a state line to get to a mall – and one without a credible anchor store, no less. Chicago, by comparison, is a shopping mecca, and I am so happy to have more options than I did back home. It is possible to dress well in Chicago…people just need to execute!

I’m hoping to visit Chicago by the middle of November. I like to shop around the Gold coast and the small boutiques in Wicker park as well. I just wanted to mention a boutique that sells Men/Women’s Italian footwear called Battaglia (on Walton) that’s worth a visit. I discovered it after going to Barney’s. The service was excellent. Styles are exclusive. I was told they were going to carry handcrafted leather coats and jackets from Italy so I will definitely stop by there in November. More often times than not one has to stop by the smaller boutiques to find a gem don’t you think?regards,Julia

i actually love this look…and wish she’d lose the belt. i love the pairing of the skin tight skirt with the looser shirt. i wish her bag was more interesting though, or that she had played with accessories…i also don’t like the shoes, i think they’re chunky in a bad way.

As a Chicago native who just moved back from NYC…. CHICAGO has blossomed in fashion, the arts and has always been on top of music. Anyhow, i know this blog is madd old, but i am real content with chicago nowadays in the summer of 2008. I have a mixture of friends here who are from Chicago, NYC, Cali, etc. and i’m sorry to say for the most part are as hip or hipper than my friends from nyc are in regards to fashion. maybe it’s just who i roll with. Yes, there is a lot of midwest trash who could care less about fashion in Chicago, but the same goes for NYC. if you just stayed bet. 23rd and 59th street in nyc, it would all be the same as the loop in Chicago. the only reason NYC is cool, hip and fashion forward is due to anything below 14th street and brooklyn. everything else is suburban. I’m not trying to compare chicago and nyc fashion; of course nyc is the fashion capital of America, but after visiting NYC last month i’ve been rethinking that. i have seen more street fashion in chicago that is avant garde, than i have in nyc lately. kudos for the blog

Oh my God, THANK YOU! I recently just moved to Chicago from Sao Paulo, having also spent a number of years in Paris and Copenhagen, and I simply must say that the lack of street style is causing my soul to wither away, I this is quite frankly a painfully unfashionable city! My fabulous pieces are molding away in my closet, I take them out to air whenever I stop by New York on business trips. Music scene? Love it. The arts? Fabulous. But my goodness, could people please start dressing better? This was posted in 2006, it’s 2009 and I have yet to see any improvements.

I simply adore your work; unfortunately, as a Chicagoan, I am rather saddened.

If you find yourself in the downtown area again soon, I'd recommend visiting S. Michigan Ave. Being a student myself, I know there are many noteworthy ensembles to be seen around Columbia, School of the Art Institute, and DePaul.

First of all, I want to say your blog is tremendously great! I'm only 15 and I enjoy looking at your blog everyday now to get tips for my wadrobe.

When I came over this article I was disappointed, but not suprised. I live in Chicago and unfortunately there doesn't seem to be the drive for fashion as it was back in the 80s as I see wih my moms old pictures. Now it's sad to say that I'm dressing a lot better than the older people here in there 30-40s. It seems that a lot of people here are just cheap. They look for the sale on 7 for all man kind jeans at Filenes, instead of paying for quality denim such as APC or Nudie. And then they think they are doing something different when they go to Urban Outfitters, that just has cheap and overpriced outerwear and accecories. We have great boutiques such as George Green, Jake, Leaders 1354,and many more that aren't visted often enough.

Its disgusting at times, but there is a bright spot in Chicago with people like me! SO please do come back and hopefully you will find the sartorial crowd. :D

Well I think your visit to Cuicago was accurate–you simply don’t see the style sensibility you see in NYC. I really think that because Chicago doesn’t have a fashion industry and no textile/garment industry we don’t have as many influences or options to mimic.

One can spot unique,individual style on occasion in Chicago, but weeks can go by before seeing someone who really turns your head, and I reside in the Bucktown area. Short of the art school and goth kids, for the most part it’s casual and conformist.

Walk down a busy street in this apparently young and hip area and you notice how many people follow trends as if they were their uniform. Young girls in their early 20s in Tory Burch ballet flats, I swear each has the same Marc Jacobs bag with the nameplate, down puffer coat, flat-ironed hair, the sorels, the uggs – recognizable brands is what I see everywhere even if many look polished and pulled together.
And it’s a wardrobe that can slide right into middle age with them safely.
I don’t often see experimentation. Seems the old ladies in the east coast are expressing themselves and having more fun than some 20-somethings in Chicago.
Also the culture in Chi can be sports-obsessed – TVs in shops and bars now are ubiquitous where as they used to be limited to sports bars – and that cultural shift is reflected in the street style.
I see more women wearing sports jerseys as evening wear.

My theory is that there’s there’s a lack of a middle ground when it comes to independent design options. Or that middle ground wouldn’t be supported or profitable.
So there seem to be two extremes in Chicago – clothing shops that exist in every suburban mall in America – or – the other extreme – Michigan Ave boutiques which carry high-end established brand like Chanel and anything under LVMH.
The middle ground – places similar to an Opening Ceremony in New York for example, where you can find unique, independent clothing, shoe and accessory designers alongside Kenzo, or a Dover Street Market – don’t exist here.

More on that thought I just posted – I actually don’t believe someone has to be in a certain income bracket and buy their wardrobe from Oak St./Michigan Ave. to express their unique sense of style, but having more attainable options in this city would help.
Even the cast-offs at consignment shops mixed it up more the way they do in Berlin, NY or London, it could help.
It’s mostly limited to well-known luxury brands, and it’s rare to find unique, European independent designers, or more avant grade designers like Commes des Garcons under the same roof.
There are some interesting vintage shops in this city but not always a guarantee you’ll something or in your size.

And the trends that are actually timeless just don’t get traction here I found.
I’ve been unable to find clog boots – not Dansko or ortho clogs but stylish ones like from No. 6.
I’ve tried to find a well-constructed pair of gaucho/culottes and surprisingly people in shops here don’t seem to even know what they are. So seems buyers are determining what would sell and a lot of things just never make it to the midwestern market.
Also sought a Schott Perfecto jacket since it’s a classic, from a luxury consignment shop in the Gold Coast and a owner didn’t know what it was either and told me they “only sell luxury brands”. I told her Perfectos were sold at Barneys to which she changed the subject and tried to push me into buying a facsimile of a moto jacket for twice the price thinking I’d probably be impressed by the designer name. But I was disappointed by the selection.

Art Institute design department has improved and although it’s not at the level of Central Saint Martins, there are some talented student designers coming out of there, and the most talented grads usually end up in in east coast. The former mayor’s attempt to turn this into a fashion destination with student designers was already DOA when the incubator partnered with Macys – a commercial department store.

Bucktown/Wicker Park has a few options (PS45 which is small but well curated, and Robin Richman) but for the most part walk around and it’s slim pickings. safe brand abound, and mall shops mixed in, and lately more and more athletic shops are taking up residency.

I do believe there could be potentially more individually stylish people in this city if it didn’t lack options.
There are blogs like Scott’s in the meantime, and others in cities globally that can fill the void and inspire.